New Bisabolane Sesquiterpenes and Coumarin from Leontopodium longifolium

Abstract

From the roots of Leontopotium longifolium, three new bisabolane sesquiterpenes, rel-(1S,4R,5S,6R)-4,5-diacetoxy-6-[(R)-1,5-dimethylhexa-3,5-dienyl]-3-methylcyclohex-2-enyl (Z)-2-methylbut-2-enoate (1), rel-(1S,4R,5S,6R)-4,5-diacetoxy-6-[(R)-5-hydroxy-1,5-dimethylhex-3-enyl]-3-methylcyclohex-2-enyl (Z)-2-methylbut-2-enoate (2), rel-(1R,2S,4R,5S)-4-acetoxy-2-[(R)-5-hydroxy-1,5-dimethylhex-3-enyl]-5-methylcyclohexyl (Z)-2-methylbut-2-enoate (3), and a new coumarin, 2,3-dihydro-5-hydroxy-2-(1-methylethenyl)-7H-pyrano[2,3-g][1,4]benzodioxin-7-one (4) together with nine known compounds have been isolated. The structures of these compounds were established by spectroscopic methods. Compounds 1 and 2 exhibited moderate cytotoxic activities against human promyelocytic leukemia (HL-60) cells.

Metabolic fingerprinting of Leontopodium species (Asteraceae) by means of 1H NMR and HPLC–ESI-MS

“…Unfortunately, m / z values of 477.1 and 459.0 could not be identified. Comparison with literature data suggested that the m / z value of 459 corresponds to a bisabolane derivative isolated from L. longifolium (= L. souliei ; Li et al, 2006). …”

“…Despite these results, nearly nothing is known about bioactive compounds in other Leontopodium species. Until now, only a few phytochemical and pharmacological investigations have been conducted on these species (e.g., Leontopodium longifolium Ling: Li et al, 2006; Leontopodium leontopodioides Beauverd: Li et al, 1994; Leontopodium andersonii C.B. Clarke: Schwaiger et al, 2010; Leontopodium nanum Hand.-Mazz.…”

Neuroprotective Effect of ent-Kaur-15-en-17-al-18-oic Acid on Amyloid Beta Peptide-Induced Oxidative Apoptosis in Alzheimer’s Disease

“…Several studies have affirmed that Leontopodium longifolium has anti-inflammation and cough abilities [36]. Persuasive evidences have substantially reported pivotal function of Aβ induced the generation of free radicals which expedite oxidative stress that contributes a lot to process of AD [37,38].…”

Natural Sesquiterpenoids

“…81 Another three new sesquiterpenes 90-92 have been isolated from the roots of Leontopodium longifolium. 82, 83 Baccharisketone 93 is another new bisabolane derivative, which has been obtained from the leaves of Baccharis dracunculifolia. 84 The active principle of an extract from the roots of Ostericum koreanum 85 which affects adults of the Dermatophagoides genus, has been identified as the known sesquiterpene bisabolangelone 94.…”